I had originally prepared the product backlog with stories that were way too large. I think that I was confusing the role of the Scrum Product Owner and the XP Customer a bit. I was worried about “being polluted.” After reviewing the Scrum planning process again, I realized that I really needed to break up the top priority stories. I took the top dozen and broke them up into around 40 smaller stories. Some I left for the team to break up as an exercise. I needed input from the team leads to break up a few of the stories, so I left them as epics. There were a few stories that defied division. These were large design tasks. We have to interface with a couple other teams and get some customer feedback, so we need to have some initial designs to present that are somewhat comprehensive. I knew that this would be difficult to incorporate in an Agile process, but it is a part of our work and I wanted to try and assimilate it. We also had some carry-over work from the previous release and some open-ended consulting that we needed to account for in our estimations. The carry-over work was interrupt-based, basically bugs found by other teams that we would need to turn around quickly. To incorporate this into the planning, I created a story at upmost priority to account for this possible work.

Given the distributed nature of the team, I decided to do the planning poker on-line. I booked some video conference rooms, but also a phone conference. Since physical cards would not work for us, we used Adobe Connect (‘natch) with a polling pod for each person to put in their card choice. I figured that most of the team would hang out in their offices and dial in to the meeting, but everyone came to the conference rooms and that actually worked really well.

I’d budgeted about 2 hours for Planning Poker. I figured that this would give us time to get into the process and go through a few sprints worth of stories. Turns out that my estimating skills on planning poker needs some work itself.

The hard-to-estimate high priority stories derailed us for a long time. Especially the open-ended consulting and bug fixing tasks. The team got stuck on estimating an unknown. It took a lot of time and a lot of frustration, but we finally reached a rough consensus and moved on to the difficult-to-split design tasks. We tried a zillion ways to split them up or come up with better estimates. In the end they got a high estimate and were tabled to the sprint planning meeting. In retrospect, even though these stories were the highest priority, I probably should have started us on the concrete tasks and come back to these later in the session. For a team’s first planning session these were some pretty tough tasks to work through.

Once we got past these tasks, it got a bit better, but it was still difficult. The team got too caught up in the details of each story, unable to make an estimate before digging deep. If there was uncertainty, we got really deep in the weeds. The 2 minute timer didn’t help. The more concrete stories that needed to be broken up took a lot more time than I expected too. Members of the team kept wanting to discuss details on each story. The scrum master and I kept trying to bring us back to the sprit of estimation, but it was a slog. After almost three hours, we had only gotten through a dozen stories, not even enough to get us through our first sprint. I’m going to look for better ways to explain the spirit and intent of Agile estimation to the team. It is difficult to grasp sometimes for detail-oriented folks.

Even though we were short of estimated stories, we went ahead with our first planning meetings anyway. One team was able to take on stories and create tasks and estimates from them. They may be a bit short of work, but they made some progress. The other team had difficulty pulling stories given the paucity of choices.

We learned some useful things today. We separated the teams to do the sprint planning, pulling from the backlog. The teams were in separate video conference rooms. I and the scrum master moved between them. We realized afterwards that we really need to have both teams together to figure out how the stories would be divided and then the teams should have separated to create their tasks and do their estimations. I was also too eager to jump into the poker session itself, and I didn’t spend enough time going through the backlog with the team and discussing my priorities. We’ll fix these issues next time.

We’ll do a second planning poker session tomorrow. Before then, I’ll take in the new stories we created in the backlog, make sure that they are prioritized correctly, and try to break up some more of the stories so that we don’t have to spend time doing that in the poker session.

I knew the first planning poker session was going to be a bit rocky as we felt our way through the process, but for me it was brutal. I know that as we gain experience it will get progressively easier and so I’m more worried about the team’s morale right now than I am concerned about the process. We’ll see how it goes.

On one hand, our super short sprints play to our advantage as it lets us try stuff out in a sprint without a huge commitment. On the other hand, it makes breaking stories up into sprint-sized chunks really difficult. It feels a bit like we’ve jumped into the deep end because of this. We’re open to making a lot of changes, but we’re hoping to keep a consistent sprint length through the cycle since modifying the duration of our sprints will make it difficult to establish a rhythm. Again, we’ll see how it goes.